Studies on Amphiprotic Compounds.14. Application of the αH Hydrogen-Bonding Acidity Scale to Complexation between Pyridine N-Oxide and Monomeric Hydrogen-Bond Donors in Cyclohexane

Journal of Organic Chemistry

Volumn 55, Issue 7, 1990, Pages 2230-2232

  Abboud, Jose Luis M ^a   Sraidi, Khadija ^b   Abraham, Michael H ^c   Taft, Robert W ^d  

^a INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c CADI AYYAD UNIVERSITY   (Morocco)

^d UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009797945     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00294a046     Document Type: Article

References (13)

1. Part 3 in this series: Abboud, J.-L. M.; Roussel, C.; Gentric, E.; Sraidi, K.; Lauransan, J.; Guiheneuf, G.; Kamlet, M. J.; Taft, R. W. J. Org. Chem. 1988, 53, 1545.
2. Abraham, M. H.; Duce, P. P.; Grellier, P. L.; Prior, D. V.; Morris, J. J.; Taylor, P. J. Tetrahedron Lett. 1988, 29, 1578.
3. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.: Taylor, P. J. J. Chem. Soc. Perkin Trans. 2, in Dress.
4. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J.; Laurence, C.; Berthelot, M. Tetrahedron Lett., in press.
5. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Morris, J. J.; Taylor, P. J. J. Chem. Soc. Perkin Trans. 2. submitted.
6. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Taft, R. W.; Morris, J. J.; Taylor, P. J.; Laurence, C.; Berthelot, M.; Doherty, R. M.; Kamlet, M. J.; Abboud, J.-L. M.; Sraidi, K.; Guiheneuf, F. J. Am. Chem. Soc. 1988, 110. 8534.
7. Frange, B.; Abboud, J.-L. M.; Benamou, C.; Bellon, L. J. Org. Chem. 1982, 47, 4553 and references therein.
8. Sraidi, K. M.Sc. Thesis, University of Marrakech, 1987.
9. Error limits for these correlations are two standard deviations.
10. Caldwell, G.; Kebarle, P. J. Am. Chem. Soc. 1984, 106, 967.
11. Private communication from Prof. P. Kebarle.
12. A more extensive correlation, involving H2O, 10a several carboxylic acids, 10a and phenols 10b leads to eq 12:
13. This is in line with recent reports on the acidity and basicity of azoles, both in the gas phase and in solution (see, e.g.: Catalan, J.; Abboud, J.-L. M.; Elguero, J. In Advances in Hetereocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1987; Vol. 41, pp 187–274).